Options Trading Journey: $6K to $100K - Week 22

Week 22 Performance Overview

• Current Account Balance: $9,115
• Trump announced 25% tariffs on Japan and South Korea effective August 1st
• More countries expected to receive tariff letters in the coming weeks
• Managed positions in $TSLL and opened new positions in $OSCR
• Continuing to maintain a cash-heavy position while waiting for pullback opportunities
• Realized gain of $1,176.55 (down -$50.09 from Week 21) realized loss from rolling down $TSLL and $OSCR while receiving net credits

Portfolio Performance

Moving forward I will also provide my portfolio performance on a weekly basis. Some context: prior to focusing on options selling, I used this Schwab portfolio for regular trading, often making poor investment decisions. Looking back, we all learn through experience. Last year, I took a significant loss on a penny stock ($BBIG), which impacted my all-time performance. Currently, I'm down about $2,011 despite contributing over $11K in deposits (last column). I began focusing exclusively on the wheel strategy in early 2024, which is why the past 1-year (+37.43%) and YTD (+24.17%) performance metrics are what truly matter for tracking this journey.

Market Recap

This week, Trump began sending out tariff letters to various countries, most notably Japan and South Korea, announcing 25% tariffs that would go into effect on August 1st. The market seemed to have shrugged this off. More countries are expected to receive similar notices in the coming weeks. Trump has reiterated that this time he will not move the deadline back, though the market seems to be taking a wait-and-see approach to these announcements.

My Week 22 Trades

$TSLL

I rolled down and out from $10 cash secured puts to $9.5 strike $TSLL on Monday following the online feud between Musk and Trump as Elon started his own political party to challenge midterm seats. I rolled down to derisk in case TSLA were to continue falling. The roll was executed for a total net credit of $4. While this doesn't seem like much, it allows me to derisk while still collecting premiums and gives me flexibility to continue rolling as needed.

• 07/07/2025 Buy to Close:
  • TSLL 07/11/2025 10.00 P
  • Quantity: 2
  • Debit: -$102
• 07/07/2025 Sell to Open:
  • TSLL 07/18/2025 9.50 P
  • Quantity: 2
  • Credit: $106
  • Net Credit from rolling: $4

Towards the end of the week, I rolled one of the contracts to 07/25 expiry, which coincides with TSLA earnings week, resulting in juicier premiums. This roll generated a net credit of $30 for the single contract. I still hold one contract expiring on 07/18 that will allow me to roll for potentially more credit if TSLA falls in the upcoming week ahead of earnings.

• 07/11/2025 Buy to Close:
  • TSLL 07/18/2025 9.50 P
  • Quantity: 1
  • Debit: -$8
• 07/11/2025 Sell to Open:
  • TSLL 07/25/2025 9.50 P
  • Quantity: 1
  • Credit: $38
  • Net Credit from rolling: $30

$OSCR

OSCR was mentioned frequently this week, but I took this trade based on chart analysis rather than hype. I identified a trendline support around $15, which OSCR broke through this week. The next level of support/demand zone I'm watching is around $13-$14. I initially sold $15 strike cash secured puts playing the trendline, and as it approached expiration and the trendline broke, I rolled down and out to further derisk while collecting additional premium.

• 07/07/2025 Sell to Open:
  • OSCR 07/11/2025 15.00 P
  • Quantity: 1
  • Credit: $15

Later in the week, I rolled down to a $14 strike expiring 07/18 for a net credit of $21. Rolling down allows me to derisk while collecting additional premium, which further reduces my adjusted cost basis and helps me manufacture a win as needed.

• 07/11/2025 Buy to Close:
  • OSCR 07/11/2025 15.00 P
  • Quantity: 1
  • Debit: -$50
• 07/11/2025 Sell to Open:
  • OSCR 07/18/2025 14.00 P
  • Quantity: 1
  • Credit: $71
  • Net Credit from rolling: $21

I also opened another OSCR cash secured put at a $12 strike expiring 07/18 for a net credit of $25. I opened this position based on the chart's demand zone near $13-$14 that I believe will serve as a bounce.

• 07/11/2025 Sell to Open:
  • OSCR 07/18/2025 12.00 P
  • Quantity: 1
  • Credit: $25

What I'm Holding Now

As of July 13, 2025, here's what's in my portfolio:

• 1 cash secured put on $TSLL at $9.50 strike (07/18 expiry)
• 1 cash secured put on $TSLL at $9.50 strike (07/25 expiry)
• 1 cash secured put on $OSCR at $14.00 strike (07/18 expiry)
• 1 cash secured put on $OSCR at $12.00 strike (07/18 expiry)
• $4,757.80 Cash reserves awaiting potential market pullback opportunities
• Weekly $100 deposit on Wed and Fri splits

Looking Ahead

I may have been a bit too cautious or have been waiting for a pullback for too long, but I'm maintaining my cash-heavy position while waiting for opportunities to arise. I'll continue to monitor my open positions in $TSLL and $OSCR, particularly as we approach TSLA's earnings week. As always, I'll be using the options scanner to identify new potential trades while managing my existing positions.